Reaktion #519229

Reaktionsgleichung

5-aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran

potassium bisulfate

sodium hydroxide

→

citalopram

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationwas then filtered through celite
2. 2
   SonstigeThe filtrate was partitioned between aqueous sulfuric acid (2 M) and toluene
3. 3
   SonstigeThe aqueous layer was separated
4. 4
   workup.ADDITIONthe pH of the mixture was adjusted to >9 by the addition of aqueous ammonia solution (25% w/v)
5. 5
   ExtraktionThe solution was extracted with toluene
6. 6
   Extraktionthis latter toluene extract
7. 7
   Trocknenwas dried over magnesium sulfate
8. 8
   Sonstigeevaporated

Vorschrift

To a stirred solution of 5-aminomethyl-1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran (0.5 g, 1.5 mmol) in dichloromethane (10 mL) was added an aqueous solution of potassium bisulfate and sodium hydroxide (19 mL; 0.2 M in K2S2O8, 3.8 mmol; 0.4 M in NaOH, 7.6 mmol), followed by an aqueous solution of nickel sulfate (1.5 mL, 40 mM, 61 μmol). The mixture was stirred vigorously for 4 days, and was then filtered through celite. The filtrate was partitioned between aqueous sulfuric acid (2 M) and toluene. The aqueous layer was separated, and the pH of the mixture was adjusted to >9 by the addition of aqueous ammonia solution (25% w/v). The solution was extracted with toluene, and this latter toluene extract was dried over magnesium sulfate and evaporated to give the free base of citalopram as a very pale yellow oil (0.35 g, 70%).

Quelle